Compositional heterogeneity may limit the usefulness of some commercial naphthenic acids for toxicity assays

Science of the Total Environment

Volumn 409, Issue 19, 2011, Pages 4125-4131

  West, Charles E ^a   Jones, David ^a   Scarlett, Alan G ^a   Rowland, Steven J ^a  

^a UNIVERSITY OF PLYMOUTH   (United Kingdom)

Author keywords

Alkylphenols; GC GC MS; Microtox; Naphthenic acids; Toxicity

Indexed keywords

ALKYLPHENOLS; COMMERCIAL MIXTURES; COMPOSITIONAL HETEROGENEITY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MICROTOX; MONOCARBOXYLIC ACIDS; NAPHTHENIC ACID; OIL PRODUCTION PLATFORMS; OIL SANDS INDUSTRY; POTENTIAL VECTORS; PRODUCED WATER; TOXIC COMPONENTS; TOXICITY ASSAYS;

BIODEGRADATION; CARBOXYLIC ACIDS; CRUDE OIL; DRILLING PLATFORMS; GAS CHROMATOGRAPHY; HYDROCARBONS; MANUFACTURE; MASS SPECTROMETRY; MIXTURES; OIL SANDS; PRODUCTION PLATFORMS;

TOXICITY;

ALKYLPHENOL; BIOCIDE; CARBOXYLIC ACID DERIVATIVE; HYDROCARBON; NAPHTHENIC ACID; PETROLEUM; UNCLASSIFIED DRUG;

ASSAY; CARBOXYLIC ACID; CRUDE OIL; GAS CHROMATOGRAPHY; HETEROGENEITY; MASS SPECTROMETRY; OIL SAND; PHENOL; TOXICITY;

ARTICLE; ASSAY; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENVIRONMENTAL EXPOSURE; MASS FRAGMENTOGRAPHY; PRIORITY JOURNAL; TOXICITY TESTING;

CARBOXYLIC ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; TOXICITY TESTS;

EID: 80051801077     PISSN: 00489697     EISSN: 18791026     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2011.05.061     Document Type: Article

References (21)

1. Barrow M.P., Witt M., Headley J.V., Peru K.M. Athabasca oil sands process water: characterization by atmospheric pressure photoionization and electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. Anal Chem 2010, 82:3727-3735.
2. Choi K., Sweet L.I., Meier P.G., Kim P.G. Aquatic toxicity of four alkylphenols (3-tert-butylphenol, 2-isopropylphenol, 3-isopropylphenol, and 4-isopropylphenol) and their binary mixtures to microbes, invertebrates, and fish. Environ Toxicol 2004, 19:45-50.
3. Clemente J.S., Prasad N.G.N., MacKinnon M.D., Fedorak P.M. A statistical comparison of naphthenic acids characterized by gas chromatography-mass spectrometry. Chemosphere 2003, 50:1265-1274.
4. Clemente J.S., MacKinnon M.D., Fedorak P.M. Aerobic biodegradation of two commercial naphthenic acids preparations. Environ Sci Technol 2004, 38:1009-1016.
5. Donkin P., Smith E.L., Rowland S.J. Toxic effects of unresolved complex mixtures of aromatic hydrocarbons accumulated by mussels, Mytilus edulis, from contaminated field sites. Environ Sci Technol 2003, 37:4825-4830.
6. Frank R.A., Kavanagh R., Burnison B.K., Arsenault G., Headley J.V., Peru K.M., et al. Toxicity assessment of collected fractions from an extracted naphthenic acid mixture. Chemosphere 2008, 72:1309-1314.
7. Grewer D.M., Young R.F., Whittal R.M., Fedorak P.M. Naphthenic acids and other acid-extractables in water samples from Alberta: what is being measured?. Sci Total Environ 2010, 408:5997-6010.
8. Hao C., Headley J.V., Peru K.M., Frank R.A., Yang P., Solomon K.R. Characterization and pattern recognition of oil sands naphthenic acids using comprehensive two dimensional gas chromatography/time of flight mass spectrometry. J Chromatogr A 2005, 1067:277-284.
9. Headley J.V., Barrow M.P., Peru K.M., Derrick P.J. Characterization of naphthenic acids from Athabasca oil sands using electrospray ionization: the significant influence of solvents. Anal Chem 2007, 79:6222-6229.
10. Headley J.V., Peru K.M., Barrow M.P. Mass spectrometric characterization of naphthenic acids in environmental samples: a review. Mass Spectrom Rev 2009, 28:121-134.
11. Johnson R.J., Smith B.E., Sutton P.A., McGenity T.J., Rowland S.J., Whitby C. Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching. ISME J 2011, 5:486-496.
12. Peters L.E., MacKinnon M., Van Meer T., van den Heuvel M.R., Dixon D.G. Effects of oil sands process-affected waters and naphthenic acids on yellow perch (Perca flavescens) and Japanese medaka (Orizias latipes) embryonic development. Chemosphere 2007, 67:2177-2183.
13. Rowland S.J., West C.E., Scarlett A.G., Jones D. Identification of individual acids in a commercial sample of naphthenic acids from petroleum by two-dimensional comprehensive gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom 2011, 25:1741-1751.
14. Rowland S.J., Scarlett A.G., West C.E., Jones D., Frank R.A. Diamonds in the rough: identification of individual naphthenic acids in oil sands process water. Environ Sci Technol 2011, 45:3154-3159.
15. Rowland S.J., West C.E., Scarlett A.G., Jones D., Frank R.A. Identification of individual tetra- and pentacyclic naphthenic acids in oil sands process water by comprehensive two-dimensional gas chromatography-mass spectrometry. Rapid Commun Mass Spectrom 2011, 25:1198-1204.
16. Rowland S.J., Jones D., Scarlett A.G., West C.E., Hin L.P., Boberek M., Smith B.E., Whitby C. Synthesis and toxicity of some metabolites of the microbial degradation of 'model' naphthenic acids. Science of the Total Environment 2011, 409:2936-2941.
17. Rowland SJ, West CE, Scarlett AG, Jones D, Boberek M, Pan L, Ng M, Kwong L, Tonkin A. Identification of naphthenic acids by GCxGC-ToF-MS: Monocyclic and monoaromatic naphthenic acids: Synthesis & characterisation. Environmental Chemistry Letters (In press) doi:10.1007/s10311-011-0314-6.
18. Shepherd A.G., van Mispelaar V., Nowlin J., Genuit W., Grutters M. Analysis of naphthenic acids and derivatisation agents using two-dimensional gas chromatography and mass spectrometry: impact on flow assurance calculations. Energy Fuels 2010, 24:2300-2311.
19. Smith B.E., Lewis C.A., Belt S.T., Whitby C., Rowland S.J. Effects of alkyl chain branching on the biotransformation of naphthenic acids. Environ Sci Technol 2008, 42:9323-9328.
20. Thomas K.V., Langford K., Petersen A.J., Smith K.E., Tollefsen K.E. Effect-directed identification of naphthenic acids as important in vitro xeno-estrogens and anti-androgens in North Sea offshore produced water discharges. Environ Sci Technol 2009, 43:8066-8071.
21. Zhang X., Wiseman S., Yu H., Liu H., Giesy J.P., Hecker M. Assessing the toxicity of naphthenic acids using a microbial genome wide live cell reporter array system. Environ Sci Technol 2011, 45(5):2936-2941.